Verfahren zur Herstellung von 5 beta-Bisnorcholanderivaten

• Main Authors: EMANUEL KASPAR,DR, FERDINAND KUHNEN,DR, MAHMOUD MUFTIC,DR, RAINER PHILIPPSON,DR
• Format: Patent
• Language: German
• Published: 04.06.1969
• Subjects: CHEMISTRY; METALLURGY; ORGANIC CHEMISTRY; STEROIDS

Novel compounds of the general formula <FORM:1118976/C2/1> or an ammonium salt thereof, in which R1 and R2 each represents a hydrogen atom or an unsubstituted or substituted alkyl, aryl, aralkyl or heterocyclic group or together represent members of an unsubstituted or substituted ring system which may also be interrupted by a further hetero-atom, Z- represents a \s7CH2, \s7CH(OH) or \s7C = O group, X represents a \s7CH2, \s7CH(OH), \s7CH(O Acyl) or \s7C = O group, C4 = C5 represents a double bond or a single bond having a 5b -H configuration and C1 = C2 and C6 = C7 each represents a single or double bond, are obtained in a process which comprises (a) reacting a 22-aldehyde of the formula <FORM:1118976/C2/2> in which X, Z and C4 = C5 have the meanings given above with a base of the formula <FORM:1118976/C2/3> in which R1 and R2 have the meanings given above, and reducing the C = N or 20(22)-double bond contained in the resulting compound, and if desired, simultaneously with the reduction, hydrogenating the D 4-double bond if present in the starting material, or (b) reducing the carbonyl group C = O of the amide in a compound of the formula <FORM:1118976/C2/4> in which R1, R2, Z, C4 = C5 and X have the meanings given above, to a CH2 group, if desired after protection of a 3-keto group in the starting material, or (c) esterifying a compound of the formula <FORM:1118976/C2/5> in which Z, C4 = C5 and X have the meanings given above, in the 22-position with a sulphonic acid, and reacting the resulting 22-ester with an appropriate base, or (d) esterifying a compound of the formula <FORM:1118976/C2/6> in which Z, C4 = C5 and X have the meanings given above, in the 22-position with a sulphonic acid, and converting the resulting 22-sulphonate ester into a 22-halogen compound, and reacting the 22-halogen compound with an appropriate base, and if desired, in the resulting compound oxidizing any 11-OH and/or 3-OH group or saponifying any 3-O-acyl group, or reducing any 11-keto group and/or 3-keto group(s) and/or D 4-double bond and/or acylating any 3-OH group, and/or, if desired, when a D 4-double bond is present, introducing a D 1- and/or D 6-double bond(s), and/or if desired, monoalkylating or dialkylating a resulting 22-amino group in which R1 and/or R2 represent hydrogen atom(s) and/or, if desired, converting the compound so obtained into a corresponding secondary, tertiary or quaternary ammonium salt. The invention also comprises the D 20(22) compounds corresponding to the above formula. Pharmaceutical compositions containing the above compounds and having bacteriostatic, fungistatic and trichomonochidal activity are administered externally, parenterally or orally.